


The Road Of Our Times

by Rainy_DayReader



Category: Supernatural
Genre: Dean Win - Freeform, Dean in Panties, F/M, Fluff, Shower Sex, Smutt
Language: English
Status: In-Progress
Published: 2017-11-24
Updated: 2017-12-31
Packaged: 2019-02-06 07:07:49
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 3
Words: 3,086
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/12812286
Author URL: https://archiveofourown.org/users/Rainy_DayReader/pseuds/Rainy_DayReader
Summary: Dean, Sam? Who are you going to choose?





	1. Side of the Road

You were fixing up your car on the side of the rode. "Fuck." You said, it was a hot day and it was taking to long. Then you heard an engine purr. Not yours but, maybe an Impala you guessed. And you were right, a black '67 Impala appeared and pulled over behind your car, a black '65 Mustang. A man about your age got out of the driver's side. You could see a gun as he bent to get out. You grabbed yours only a few inches away. He got closer not saying anything. He was attractive looking, very attractive looking. He still said nothing, you thought it was strange. You fired your gun into shoulder, not enough to kill him, just enough to hurt him. "Fuck! What the hell man?" He yelled at you, in pain, grabbing his shoulder. Then another attractive man got out. Very tall, but looked younger than the other man. Brothers you would guess. "Dean!" Yelled the younger one. "I'm sorry, but when someone comes over to me and doesn't say anything. I find it a bit weird. " You said shrugging. "Doesn't mean you have to shoot me!" He said.  
"You'll be fine." You said rolling your eyes.  
"I'll fix you up, just give me a minute." You said.  
"Wait. Who are you anyways?" Dean, says still in pain.  
"Names Y/N, Winchester." You said. he looks at you confused.  
"It's my job to know, and killing things, but mostly knowing things." You said, grabbing the first aid kit in the car. "Just keep pressure on it." Sam said.  
"I'm not an idiot Sam!" He said, clearly trying to make himself tougher looking. You chuckled. "Let me look at you." You said, you took off his shirt. You didn't really need to but you really wanted to see what he looked like underneath. You smiled when you saw the very nice six pack. "Impressed?" He raised an eyebrow. You pressed your finger to the wound, he grunted. "Oops." You said sarcastically. You sewed up the hole and cleaned off the blood. "So are you a hunter?" Sam asked. You smiled and pulled down your collar, exposing your anti-possession tattoo.  
"So that's a yes." Dean said, grunting as he stood up.  
"So Winchesters, you gonna help me or what?" You asked them, wiping your hands off on your shirt. "Yeah." Dean said. You looked over the hood, "I was thinking the spark plug was worn out, but that wasn't it. It might be clogged radiator." You said. Dean stack his head in, "Hmm. I-hold on." He said looking through it. "Yeah, it's a clogged radiator. Easy fix." Dean said and he started to work on it. You smiled and backed away, you knew it was an easy fix. You could do it yourself, but it was hot and Dean might take his shirt off so you decided to grab a beer out of the cooler and enjoy the show. Sam sat next to you on the ground, you handed him a beer.  
"So what are you doing out here?" Sam asked as you watched Dean take off his shirt and wipe his forehead with it. "Hmm? I um...there was a hunt. I just got done." you said. You took a sip of your beer. "Why are you here?" You said turning to Sam.  
"Came from a hunt a few towns over, just passing through.  
"Cool." You said, grabbing another beer and walking over towards Dean. "How she looking?" You asked the sweaty man.  
"I'm just cleanin' up." He said holding out his hand for the beer, you chuckled, took a sip. Handed it to him and pulled it away before he could grab it. You gave him a fake pouty lip. You walked away, you paused and turned around. Giving him a smile. He shook his head and smiled. He closed the hood a few minutes later.  
"Alright good to go." He said, taking the beer you handed him.  
"Thanks." He said  
"So, you boys headed to a new hunt?" You asked, hoping they would take you. You were itching to go on another one.  
"No, home." Sam said.  
"Home?" You said.  
"Yeah we live in a b-" Sam said, but was cut off by Dean said jabbing him in the gut.  
"Don't worry. I um totally cool with you not telling me." You said rolling your eyes once again. "You got a place to stay?" Dean asked.  
"Motels and my car." You said. "Look, I'm not offended that you don't want to invite me home, you've known me for two-three hours and I shot you." You said, Sam got up and walked back to the car.  
"I'm offended that you haven't made a move on me yet." You said whispering in Dean’s ear. He was shocked as you whispered into his ear, your warm breath hitting him like fire. He coughed. "I um...You see." He tried to say.  
"I thought you were a charmer of all the ladies." You said. HE smiled.  
"Later." He said, slipping you his number. You smiled. He stood up, and held out his hand. You took it.  
"So." You said.  
"See you around." He said. He turned around, you slapped his ass. Making Him jump.  
"Damn, call you later." You mouthed. He smiled and walked away.


	2. Room 308

It was a few hours later, it seemed like a good idea to call that sweet ass Dean.

"Hello?" Said a very masculine voice.

"Hey, it's Y/N. I'm in room 308 at the Star Hotel. See you soon." You said confidently.

"Okay wha-" "Soon." You said hanging up the phone. You smiled to yourself and walked over to the door. Unlocked it and undressed. Making your way to the shower. "Okay.." you murmured. The shower was ready, the warm water hit your skin. The steam filled the room, you hadn't noticed the cold brush of air when the door opened. You turned around, there was a muscular man standing there. "Was wondering when you were gonna show up." You said bluntly, reaching for the shower soap. Dean grabbed your wrist and stopped you, you looked into his green eyes and smiled. "I like a man who takes control." Your eyes trailed down, past his toned stomach down to his v-line and then to his cock. You gasped as quietly as you could, it was long and thick. Bigger than anything you'd seen. He coughed, making you look back up at him. You kissed him, passionately. Your bodies brushing together, you felt him become hard underneath you. His hands traveled down your backside, down to your ass. The rested just above there while your kisses became more heated. Tongues entwining, teeth coming into the mix, while the water fell down on you. Dean's hands squeezed your ass and you moaned in pleasure. He smiled under the kisses. Dean's cock teases your already wet pussy. He picked you up and you wrapped your legs around his waste. Your mouths never leaving, only for tiny breaths of air. His throbbing cock rubbed over your clit, a louder moan slipped from your mouth, Dean seemed to swallow it. He paused for a moment, but his foot slipped and you both went crashing down, you were still clung together as the curtain went down with you and his body went over the side of the tub. The both of you were tangle with each other and the shower curtain. Then he started laughing. Really hard. You looked at the situation and started laughing too. He got up, and yelps in pain. "You alright?" You ask with a concered look on your face.

"Mother fucker. I think I sprained it. " He says his face twisted in pain.

"Shit. Looks like no sex for you." You said a smug look on your face.

"No, I'm fine. Just let me get a wrapped up." YOu rolled our eyes "Nope, I'm gonna clean up here, and your're ganna call your brother." He limped out of the room and you got up, turned off the shower, threw the curtain up over the shower rod and walked to the bedroom to find Dean standing on one foot looking at something on the dresser.

"Such a cute ass." You said leaning against the door frame. He gave you a smug smile, holding up and embarssing photo of you from yor failed collage days. Running over to Dean, your boobs bouncing painfully, and tried to grab it from his hands. He held it up high where you couldn't reach it. Your boobs rubbing against him. He looked down at them, and was distracted for a second. You climbed him and grabbed for it. He put you down on the bed.

"So...This is what you used to look like?" Dean says standing over you, looking down in embaresment, only to find his large cock. "Hey, wanna look at me? I'm talking to you." He says imatentaly. "Sorry...But yes. I was a total dork."

"Really? I think you're hot." You looked at the photo, a small smile your usall jeans and a leather jaket. But your boobs were kinda out, never really did that. Sorta a emo/punk thing going on. It was when you first got the Mustang. You didn't have many friends, but it was more than you had now. Your hair was kinda like Drew Barrymore in the 90s, but with h/c hair. Maybe it wasn't your best stage, but it wasn't that bad.

"Well, you are one atractive goth."

"Hey! I was a punk/emo...thing." You said sacrastically.

"Sure." He set the photo down and kissed you, pushing you down on the bed. "Hi..." You say breathless.

"Wait...no. No sex. You are injured. Since you won't call your brother I will." You rolled him over and got up. He grabbed your wrist and pulled you back to him. Giving him a poutly lip you sighed.

"Sorry." Dean lean his head back.

"Please..." He pleaded.

"Maybe next time." You said hissing his abs, his cock getting hard the closer you got to it. He groaned when you left. You found his phone in the pocket of his pants. He should get a passcode. You seached through to find the contact; Sam. You texted the number.

 _*Hey, sprainned my ankle, mind hitching a ride to pick me up?_ * You sent the text.

A few minutes later _._

 _*Sure, but what happened?*_ Sam texted back

_*Tell you when you get here.*_

You shut off his phone and grabbed his clothes. Dean had grabbed the photo once again as was starung at it, you plucked the photo from his hands and threw the clothes down. "Yuo sure?"   
"Sorry. Just texted your brother. He'll be here soon _."_

"Damn..."

"Well, you got my number now. So maybe another time. Now get dressed." You said slapping his thigh. 

"Fine." He gets dressed and you put on a robe. Sam showed up and helped Dean into the car. You smirked as he limped away. 

 

 

**Notes for the Chapter:**

> There's this really, really, attractive guy in a few of my classes. And I don't know if he has a girlfriend, I hope he doesn't, and I think I see him look at me. But I don't know if it's at me or what. I knew him in second grade and we were super close friends. I don't know if he remembers me from then, not the point, but he's got these sexy veins on his arms and his hands. And his so damn sexy. And he was talking to my friend Joe who sits in front of me, they were talking about how I'm always on my phone (Though I'm not, I usually just listen to music) and the super sexy guy said "She's always on her phone." And he looked at me, and gave me this sexy smile. (God, I thought I was melting.) I should talk to him, shouldn't I? 
> 
> I just needed to rant, none of my friends like this guy, and needed to tell someone. Even if no one cared. 
> 
> Also hopped you enjoyed this chapter, I really enjoyed writing it.


	3. Chapter 3

**Summary for the Chapter:**

> Dean and you finally get together.

       Your phone rang, the loud noise driving you crazy. Your hand flew to where you thought it was, only to find nothing. “Shit.” You muttered. You reached farther to get it, but you couldn’t find it. Reaching farther you fell off the bed. Your body fell to the ground, the uncomfortable carpet hit your face. It was very itchy, but you were too tired to care. As soon as you started to drift off your phone rang again. “Ugh.” You saw the phone, and grabbed it.  
       “Hello?” You said, your voice quiet, still sleepy.  
       “Y/N?” Said a woman’s voice, or maybe it was a teenagers, it was too early to go  
through your head.  
       “Who is this?” You were still on the ground, not moving.  
       “I got your number from my father Joshua Campbell, look I need your help.”  
       “Josh? Sure, where are you?” You got up, groaning in pain.  
       At Bobby Singer’s. Please hurry.” She hung up before you ask who the hell Bobby was and where he was. “Crap.” You hurried around the room icing up your things and getting dressed. You hopped out the door and into the car. “Who the hell is Bobby?” You said out loud to yourself. You picked up the phone and dialed a number. “Hey, ready to pick up where we left off?” Asked Dean.        “No. I um...Who is Bobby Singer?”  
       “Bobby, oh he’s a hunter. A good guy, why?”  
       “A friend of mine...she’s over there. Where is he?”  
       “Why do you need to know?” He asks.  
       “Dean I swear to god if you don’t tell me...we are not finishing where we left off.” You said proudly, hoping to tease him.  
       “Okay. Okay. Fine, he lives….” He told you the address and you wrote it down on your hand. The car started, and you drove down the rode. It never seemed to end. The windows rolled down made the car feel less stuffy, the rental, (stolen ‘75 buggy) was different and uncomfortable compared to the Corvette you usually drive. I’m On A Highway To Hell. Came on. “You know it, baby!” You yelled jokingly.  
       “Josh!” You yelled as you saw Joshua run out of the house.  
       “Y/N you gotta go go now!” He yelled waving you away. You gave him a weird look, then he started shoving you back to the car.  
       “What the hell is going on?” You said, Josh opened the door and shoved you inside. He closed it and ran off again. You, being well...you didn’t listen. You ran off towards the house, your feet hitting the rock. Going past the cars and trucks, going inside the house. My best friend for years was in a seat, dead. Her throat was slit. Tears started to pour over, but you blinked the away. Don’t cry. Not here. Not in front of these people. You thought to yourself.  
       “Y/F/N?!” Your voice breaking. Josh held you at your shoulders. “NO!” you screamed. The tears came and you didn’t care. Trying to shake him off. “Let me go!” You kicked him and ran to her.  
“No. No.” You cried. She was dead, wrapping your arms around her, it seemed like the only thing you could do. Blood covered your shirt. Still warm. She was still warm. “You son of a bitch! What the hell did you do to her?!”  
       “Y/N...Please. We didn’t she did it to herself. Rather a demon did.” Josh said. Your heart broke. This was the only person who you could trust. Really trust. You stormed out, tears streaming down your face. The car started and you drove, never wanting to look back.

*DAYS LATER*

The pain washed away soon. You knew she was with her mother and she was better off wherever she was. It was better knowing that she wasn’t in this life anymore.  
       “Hey. Call me back.” Said Dean’s voice. Your voicemail was filled with different names. Josh, Sam, Dean.  
       “Hey.” You said quietly.  
       “Hey. We all thought you had died or something.” He laughed.  
       “Dean. Do you want to come over?” You tried to be seductive.  
       “Oh God yes.” He was already out the door. You could hear his feet hit the pavement and a door slam shut. “Be there in twenty.” He said after you told him where you were. You turned on the radio, rock. Of course. And just like he said, twenty minutes later there was a knock at the door. “Hey.” Dean said as you opened the door. You kissed him. You ran his finger through your H/C hair. You pulled him by the collar and he closed the door behind him. “I’ve waited a long time for this.”  
       “Like three weeks.” You rolled your eyes.  
       “Whatever.” His lips met yours. The song Crazy B*tch, came on. Dean’s hands went to your ass and he pulled you up. You wrapped your legs around him. He walked over to the bed and threw you down. Dean threw off his shirt, as did you. He got on top of you, careful not to put any weight on you. "This song slightly describes me." You smiled. "Crazy bitch, you fuck so good I'm on top of it." Sang Dean. "Really?" HE lifted up an eyebrow.  
       "Yes. I'm one crazy bitch."  
       "Well let's see you work." He said.  
You worked on his pants, as he worked on your mouth. Boy, he could do wonders with his tongue. You moaned with pleasure, into his mouth. Dean smiled with satisfaction. He kicked off his shoes and shoved off his pants. Dean pulled off your pants and threw them across the room. He started at your body, though it was the third time he had seen you naked, like it was the most precious thing on earth. You blushed. No guy ever looked at you this way. It was a nice change of pace.  
       “You look beautiful.”  
       “Dean…” Before you could say anymore he kissed you. His mouth moved from your lips to your jaw, then down your chest and your stomach. Dean’s gentle lips, grazed over your body. He pulled off the underwear you had been wearing with such force they ripped.  
“Those were expensive.” You said just before his face went down into you. “Oh. God.” You moaned with pleasure. Dean smiled as his tongue entered you. He lapped and kissed at your sensitive clit. “So wet for me.” He hummed. The pleasure was so intense all you could respond with was a loud moan. “Dean please…”  
       “Please what?” He said with a seductive smile.  
“Please fuck me..”  
       “As you wish.” He lined up at your entrance and teased you pussy. “You arrogant bastard!” You joked. Dean pushed in, making you yell in surprise. “Dean!” You yelled as he pushed in deeper. Dean went down for a kiss. He was nice and slow. The kiss was hot and heavy. Dean slowly went in and out. “Oh god…” He hissed. Dean’s beautiful emerald eyes traced your face. “Dean..”  
       “Let go. Just let go.” He whispered in your ear. That was all it took to send you over the edge. You shuttered through your orgasm. Dean held on to you. He kissed you and said your name over and over. When it was over, Dean rolled to your side. “Was it worth the wait?” You asked, breathless. “Oh yeah.” He whispered.  
       “Ready for round two?” Dean asked, you rolled on top of him giggling.

**Notes for the Chapter:**

> It's been awhile I'm sorry. It's been hard to find motivation and some days get out of bed. There was a comment that did help me write this. Knowing people do like what I write helps but most days it doesn't. My depression takes over my life. And all I want is to be happy and to make other people happy. My birthday is tomorrow and I can't even be happy about that. So I am sorry that it takes me so long, I am trying. I would love to take requests, I just need a distraction. Love you guys.


End file.
